M5793

Sigma-Aldrich

3-Morpholinosydnonimine hydrochloride

(consistent with structure, NMR)

Synonym(s):
SIN-1 hydrochloride, 3-(4-Morpholinyl)sydnone imine hydrochloride, Linsidomine hydrochloride
Empirical Formula (Hill Notation):
C6H10N4O2 · HCl
CAS Number:
Molecular Weight:
206.63
MDL number:
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

assay

(consistent with structure, NMR)

storage temp.

−20°C

SMILES string

ClH.NH-c1cn+(no1)N2CCOCC2

InChI

1S/C6H10N4O2.ClH/c7-6-5-10(8-12-6)9-1-3-11-4-2-9;/h5,7H,1-4H2;1H

InChI key

NCGICGYLBXGBGN-UHFFFAOYSA-N

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Packaging

25 mg in poly bottle
100 mg in glass bottle

Biochem/physiol Actions

Liberates nitric oxide (NO) spontaneously when in solution, activating guanylyl cyclase and causing an increase in cyclic-GMP. This product is a vasodilator and inhibits platelet aggregation. Using molecular oxygen, it generates both superoxide anion and nitric oxide that spontaneously form peroxynitrite.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
H de Groot et al.
FEBS letters, 315(2), 139-142 (1993-01-04)
SIN-1 which spontaneously decomposes to yield nitric oxide (NO.) and superoxide anion (O2.-) radicals caused a loss of microsomal alpha-tocopherol paralleled by the formation of alpha-tocopheryl quinone. The loss was partially prevented by superoxide dismutase but not by catalase. The...
Mushfiquddin Khan et al.
Journal of neuroinflammation, 8, 78-78 (2011-07-08)
Traumatic brain injury (TBI) induces primary and secondary damage in both the endothelium and the brain parenchyma, collectively termed the neurovascular unit. While neurons die quickly by necrosis, a vicious cycle of secondary injury in endothelial cells exacerbates the initial...
Tangying Lu et al.
The Journal of clinical investigation, 121(10), 4015-4029 (2011-09-14)
Cancer immunotherapeutic approaches induce tumor-specific immune responses, in particular CTL responses, in many patients treated. However, such approaches are clinically beneficial to only a few patients. We set out to investigate one possible explanation for the failure of CTLs to...
S Chandra et al.
British journal of pharmacology, 165(2), 506-519 (2011-07-12)
NO produced by endothelial NOS is needed for normal vascular function. During diabetes, aging and hypertension, elevated levels of arginase can compete with NOS for available l-arginine, reducing NO and increasing superoxide (O(2) (.-)) production via NOS uncoupling. Elevated O(2)...
Fabiana Blanco et al.
Diabetes & vascular disease research, 15(4), 302-313 (2018-03-04)
Despite vast clinical experience linking diabetes and atherosclerosis, the molecular mechanisms leading to accelerated vascular damage are still unclear. Here, we investigated the effects of nuclear factor of activated T-cells inhibition on plaque burden in a novel mouse model of...
Articles
Nitric oxide (NO) as a signal transporter in neurons, endothelial cells and in the immune system.
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